Replay: Amy Winehouse’s ‘Frank’ has ‘Sent Me Flying’

My relationship with Amy Winehouse’s music began with a wig. 

On a notable October morning during my first year at Loyola, my roommate Josh eagerly burst through the door with a package in their hands. Beckoning me down from my loft bed, I peered inquisitively at the purchase — a vacuum-sealed bag donned with bold, black lettering spelling out “Rehab Wig.”

Their plan was to dress as Winehouse, who I knew little of, for Halloween. At the time, I’d only listened to some of her sophomore album “Back to Black.” 

I came across her 2003 debut album “Frank” after scrolling through her discography on Spotify. I was intrigued by the name and its cover depicting Winehouse walking two small dogs on a dark street. I have a circulation of a few albums that I listen to when I feel anxious or sad, and “Frank” joined that list soon after I found it. Winehouse’s commentary regarding relationships and social life are matter-of-fact and relatable.

After pressing play, the listener is brought into a vibrant environment filled with sunny instrumentals and eccentric vocals.

The album opens with “Intro / Stronger Than Me.” Soft and sporadic guitar strums accompanied with Sarah Vaughan-inspired scat vocals set the stage for a heavily jazz influenced record. 

The latter half of the song follows with a blend of upbeat guitar and trumpet. Winehouse sings about yearning for a masculine partner who exudes the tough guy stereotype.

“Why’d you always put me in control? / All I need is for my man to live up to his role,” Winehouse sings.

The record continues with “You Sent Me Flying / Cherry,” where the former employs blunt lyricism depicting a rejection from a man much older than her. Winehouse utilizes abrupt vocal highs and aggressive runs to convey a turbulent mind. 

“Cherry” is an ode to Winehouse’s guitar. Energetic strums and softer vocals convey adoration toward playing the instrument. Though each part of the track is strong independently, the contrast between intense and delicate vocals is awkward, and the transition between the two parts is rushed.

“Know You Now” portrays a relentless impulse to get to know someone better, the irreplaceable connection to a stranger. The song’s lively flute and sultry twang emit a youthful bounce, making it particularly appealing to listeners in their 20s.

Amy Winehouse wasn’t known for restraining vulgarity in her songwriting or her everyday vocabulary. “Fuck Me Pumps” confirms this.

“Fuck Me Pumps” is the epitome of Winehouse’s incorporation of the R&B sound, with bright, feathery chords juxtaposing sardonic lyrics about a promiscuous woman seeking male validation.

“He could be your whole life if you got past one night / But that part never goes right / In the morning you’re vexed, he’s onto the next / And you didn’t even get no text,” Winehouse sings.

Each song bears thematic similarities regarding relationships. Yet, the narrative of “Frank,” isn’t entirely cohesive, covering topics ranging from infidelity to a beloved pet.

“I Heard Love is Blind” is a slow acoustic song with less arduous vocals. It doesn’t depict an actual event, but a hypothetical conversation about infidelity with a romantic partner. 

“Moody’s Mood For Love / Teo Licks” is a cover of Eddie Jefferson and James Moody’s 1952 jazz song. Winehouse’s distinct enunciation of words provides an indescribably unique twist on the standard jazz sound.

Growing up under the musical influence of jazz, I was surprised to see “(There Is) No Greater Love” covered on the album. My appreciation stems from the tastes of my father, who introduced me to Billie Holiday. “(There Is) No Greater Love” has always been one of my favorite of Holiday’s songs, and hearing a cover by Winehouse brought me back to sitting in the yard with my father and a glass of iced tea. Her version proves that she is first and foremost a jazz singer. 

I have a vivid memory of hearing “In My Bed” for the first time while shaving my legs in my San Francisco Hall communal bathroom. I fell in love with the catchy chorus and Winehouse’s confidence. I saw her as a woman unafraid to share her opinions — this inspired me to do the same.

“You’ll never get my mind right / Like two ships passing in the night,” Winehouse sings.

“Take The Box” details returning a box filled with an ex-partner’s belongings to their apartment — an experience I know all too well. Considering the subject matter, the classic R&B composition fuels Winehouse’s dejection. The velvety horns support Winehouse’s vocals and create a melancholic symphony.

“October Song” recalls the death of Winehouse’s pet bird, Ava. Her love for the canary creates a gentle tune about cherishing memories and working through grief.

“What Is It About Men” is my favorite song on “Frank.” It refers to her relationship with men in regards to the relationship her parents had. It evoked memories of my own destructive relationships and drew me into reflecting on these feelings.

“Emulate all the shit my mother hates / I can’t help but demonstrate my Freudian fate / My alibi for taking your guy / History repeats itself, it fails to die,” Winehouse croons.

As soon as I heard the song, I knew it was destined to be on repeat for the foreseeable future. If I was walking to class, this song was likely playing in my headphones. I remember sitting at my desk analyzing the lyrics, trying to break through its complexities. 

Winehouse’s infatuation with men continues on “Amy Amy Amy / Outro.” It implements classical jazz elements as well as soul and R&B. 

“My weakness for the other sex / Every time his shoulder flex / Way the shirt hangs off his back / My train of thought spins right off track,” Winehouse sings.

It makes the perfect closing to an album that brings listeners on a tumultuous joyride through the mind and experiences of Amy Winehouse. 

“Frank” has a permanent spot on my Spotify account. It always brings me back to laying on my loft bed and being so encapsulated by an artist that I had never given a chance before.

I’m so glad I gave Winehouse a chance.

“Frank” is available on all major streaming platforms.

Replay is a recurring music review column.

Featured image courtesy of Island Records.